Monoazo dyestuffs of low water-solubility



United States Patent 3,206,453 MONOAZO DYESTUFFS 0F LOW WATER-SOLUBILITY Ernest Merian, Bottmingen, Basel-Land, Switzerland, Bruno J. R. Nicolaus, Milan, Italy, and Otto Semi, Arlesheim, Basel-Land, and Walter Wehrli, Riehen, Basel, Switzerland, assignors to Saudoz Ltd., Basel, Switzerland No Drawing. Filed June 12, 1963, Ser. No. 287,221 Claims priority, application Switzerland, Aug. 13, 1959,

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with a pyrazolone of the general formula OH Ec=t l \N lower alkyl C=N NE-SO2N H3 ower alkyl (III) preferably at pH values above 7 and especially at 7-12, in the manner described in the examples.

76,919 10 The new monoazo dyestuffs of low water-solubility dye 6 'Clallnsfrom aqueous dispersion synthetic polyamide fibers such The present application is a continuationdmpart of as nylon and Perlon (registered trademark); cellulose pending application Serial 48,831 filed Aug 11 ester fibers, e.g. secondary cellulose acetate and triacetate; 1960, now Patent 3,134,766. 15 polyvinyl fibers; acryl c and modified acrylic fibers, es-

This invention relates to new monoazo dyestuffs which Peclany polyaciiylomlnlefibers Polyester fibers Prefer are of low water-solubility and which correspond to the ably terephthahc ac1d ester fibers Such Terylene, general formula Dacron, Dacron 64, Kodel and Vycron (registered trade- R marks) in yellow or orange shades. The dyestuffs can OH (I) also be applied to the same fibers by padding or printing RF techniques. They have good building-up properties on these fibers. The dyeings and prints possess very good R R3 I -Q lower alkyl fastness to light, gas fumes, washing, heat-setting, pleatg= ing, sublimation, perspiration, water and sea water, and

a 1 1k 1 are dischargeable. A fairly good reserve of viscose a (fwera y rayon, cotton, and wool is obtained, especially on after- Ill/111s formula represents hydmgen, Chlonne, treatment with a hydrosulfite. The new dyestuffs are 1111116., fluol'lne 11130, lower alkyl y ethyl also suitable for coloring lacquers, oils, plastics and arbutyl) lower alkoxy methOXY, ethoxy P P tificial fibers in the mass. Cellulose acetate and triacetate IOWPY alkanoyl zfcetyl or pmplonyng lower alkanoyl' dyed in the dope with these dyestuffs have high fastness lam-mo (e.g. acetylammo or propionylammo), lower carbto light, Washing, perspiration, gas fumes, cross dyeing,

y (F- carbmethoxy, 'cal'bethoxy and P P Y alkaline bleaching, oxalic acid, dry cleaning and peroxide the radlcal NH"cOO'1Wer alkyl leaching, and excellent fastness to Water, sea water,

NH C0OCH3 soap baths, crocking, declatizitrlig and pressing.

In the following examp es t e parts an percentages are gmfiggg gg 22 z ggsii by weight and the temperatures in degrees Centigrade. and R and R each represent hydrogen, chlorine, bro- EXAMPLE 1 mine, nitro or methyl.

The radical 15 parts of 1-ammol-acetylannnobenzene are dlazolower alkyl 40 tized 1n the normal maner with 7 parts of sodium nitrite.

The solution of the diazo compound is run at 0 into a NH-SOFN solution of 29.6 parts of 1-(4'-dimethylaminosulfonyllower alkyl amino)-phenyl-3-methyl-S-pyrazolone in 13.5 parts of is. connected to the nucleus in one of the positions 3 or 30% soffium hydroxide solution ar 1d 200 Parts 4'. Lower means that the radicals designated by this A sohmon of 40 P i of crys'tanlzed d1umf1cetate 1S term contain 1 to 4 carbons, and particmarly 1 to 2 also added to neutralize the mineral ac1d react on. The

carbon atoms. The dyestuff molecule contains no more dyestufi so formed 15 Separated and re'crystalhzed from than 2 nitro groups and no more than three halogen ethanol It melts at 213-21903 YFHOW dyemg? of atoms but it may contain other substituents in addition to ceu'ent fastness are Obtalmd wlth 1t Synthetic Poly 1 or 2 nitro groups and to 1 to 3 halogen atoms. amlde and P1Yeter fibers' The process f the production f h new dy t ff In the following table further monoazo dyestuffs are comprises coupling a diazotized amine 0f the general malted w f b5 Produced an analogous manner formula as described in Example 1 and which are suitable for R4 dyeing synthetic polyamide fibers and other artificial fibers. I They correspond to the Formula I and are characterized by lower alkyl, the position of (lower alkyl) NSO NH, R R R and R and by the shade of their dye- (H) ings on artificial fibers.

Table Shade of Example Lower Position of (lower alkyl); R1 R R3 R4 dyeing on No. alkyl N-SO2-NH- artificial fibers 4' Cl Fr H H Yellow 4' Cl 01 H H Do. 4' 01 Fr 01 01 Do. 4' H- o1 l-T 01 Do. 4' N0 H u H Do. 4' N00 Fl Fl 01 Do, 3' NO FT Fl N00 DO. 3 N0 T-T c1 01 Do. 3' NO 01 H 01 Do. 3' C H W NO: D0.

Table-Continued Shade of dyeing on C'Ph C'Fl'a 4. Dyestufi of the formula Position of (lower alkyDa Lower alkyl CHa CHa.

Example No.

We 'claim: 1. Dyestuft of the formula References Cited by the Ex 3. Dyestulf of the formula r a z mim x Mflfl E S m E m m m Tmm n m d m S R a RG m E91. R 156 A N WU P U11 B 53 S 92 Nam 23 C 0 6 m m C G 

1. DYESTUFF OF THE FORMULA 